Trump applies Venezuela playbook to Cuba, but results may differ

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President Donald Trump’s strategy toward Cuba is drawing comparisons to the earlier U.S. campaign aimed at Venezuela, with experts pointing to a familiar combination of escalating threats, economic pressure tied to oil and energy, legal steps aimed at figures in power, and a visible U.S. military footprint in the region. But those similarities are not expected to produce identical outcomes, given differences experts said exist between the two countries and the way the United States can translate pressure into political change.

Brian Finucane, a senior adviser with the International Crisis Group and a former State Department lawyer, said Trump saw the Venezuelan intervention as a “fantastic success” and has tried to replicate it elsewhere. Finucane said the approach has also been sought in other contexts, while adding that Cuba, like Iran, is “a very different country than Venezuela.” He argued that there is no clear successor structure in Cuba comparable to what followed the capture of Venezuela’s leadership.

Finucane pointed to a major contrast in leadership dynamics between the two cases. After the United States captured Venezuela’s President Nicolás Maduro, Delcy Rodríguez stepped in “with U.S. approval and remains in power,” Finucane said. By contrast, Cuban officials who spoke to The Associated Press on condition of anonymity said, “there is no Delcy in Cuba,” underscoring the lack of a similar figure that could take over with U.S. backing.

Experts also said differences in U.S. military posture matter. Finucane said the number of American forces in the Caribbean Sea now is smaller and “far less foreboding” than the larger military buildup off Venezuela in the months ahead of Maduro’s removal. He also described the possible impact of legal steps as different in each case, saying an indictment against a 94-year-old former Cuban leader, Raúl Castro, would be “less impactful” than charging Venezuela’s sitting president and using that to justify his capture.

The Associated Press report laid out multiple parallels and distinctions. It said Trump began to lay groundwork for intervention in Venezuela with escalating threats months before military action took place, including warning Caribbean leaders to “get in line or face American might.” The report described Trump standing in Florida with top national security advisers and delivering what it portrayed as one of his last public threats to Maduro ahead of the operation that removed him.

The threat messaging then carried forward into talk about Cuba. After Maduro was brought to the United States to face trial, Trump shifted his focus to other countries in the region, including Cuba, which he said in January was next. In a Reuters-style paraphrase within the AP account, the report said Trump told reporters on Jan. 5, “Cuba is ready to fall,” adding that “Cuba looks like it’s ready to fall,” and that he did not know whether it would “hold out.” The report also said Trump threatened tariffs on countries that supply oil to Cuba and said the United States might have “the honor of taking Cuba” following military operations in Venezuela and Iran; in a later repetition, the report said he called Cuba “a failed country.”

The report described U.S. oil embargoes as another area of resemblance, though it said they aim to produce opposite outcomes depending on the country. With Venezuela, the Trump administration focused on targeting oil exports to starve the Maduro government of revenue, the AP said. After Maduro’s ouster, the emphasis shifted to denying Venezuela the ability to export oil to certain countries, including Cuba, and requiring Cuba to accept U.S. conditions for shipments, the report said.

In Cuba’s case, the AP account said the embargo seeks to starve the energy-strapped country of oil imports, while allowing limited shipments to continue arriving on the island. It said the U.S. policy, as an extension of a long-standing U.S. blockade on Cuba, has made it harder for Havana to provide electricity and gasoline. Finucane told the AP that the measures could go too far and prompt some Cubans to travel toward Florida by boat, comparing the risk to patterns seen in the 1990s. He also said Trump “especially cares about immigration” and suggested that pushing too hard on Cuba could destabilize the island and raise the possibility of a refugee crisis.

Legal escalation is another parallel the report highlighted, with charging playing a role in both campaigns. The AP account said the Justice Department charged Maduro with narco-terrorism conspiracy and other counts during Trump’s first term in 2020, and that the case was later used as part of the rationale for capturing Maduro. It said Maduro pleaded not guilty and was in New York awaiting trial, and it described the move as changing Venezuela’s relationship with the United States by allowing certain sales of previously sanctioned Venezuelan oil to U.S. companies and on global markets.

In Cuba, the AP report said the immediate aim of charging Raúl Castro over the 1996 shootdown of civilian planes flown by Miami-based exiles is to step up escalation in the U.S. pressure campaign. William LeoGrande, a professor specializing in Latin American politics at American University, told the AP that charging Castro is a further move in the campaign, but argued that capturing him after charges that include murder and destruction of an airplane would not change the day-to-day operations of the Cuban government. LeoGrande said Castro “still has influence and the leadership seeks his opinion on major decisions, but he is not running the government on a day-to-day basis.”

The report also described differences in how U.S. forces were deployed ahead of the Venezuela operation compared with the current posture in the Caribbean Sea. It said that, in the months before Maduro was captured, the United States dispatched a fleet of warships near Venezuela in what it characterized as its largest military buildup in Latin America in generations, including the USS Gerald R. Ford aircraft carrier and three amphibious assault ships carrying about 2,000 Marines. The AP report said U.S. forces spent months attacking small boats accused of smuggling drugs, while fighter jets flew over the Gulf of Venezuela, and that the actual mission to capture Maduro involved more than 150 aircraft launched across the Western Hemisphere.

According to the AP, the U.S. military now has a smaller force in the Caribbean Sea, though it still includes two amphibious assault ships with Marines onboard. It also said the United States touted the arrival of the USS Nimitz aircraft carrier and accompanying warships on the same day the Castro charges were announced, while adding that the Nimitz is on its last-ever tour, participating in maritime exercises before being decommissioned.

Finucane said those distinctions make it difficult to assume the same result will follow. He told the AP that “they’re very different situations” and said a “snatch-and-grab raid against Raúl Castro or someone who’s actually in a leadership position” does not appear likely to have “the same outcome in Cuba as in Venezuela.” The AP report also cited Havana-based author Andrea Rodríguez contributing from Cuba.